The synthetic method of p-thymphenyl phenyl serine ethyl ester and p-thymphenyl phenyl serine ethyl ester

A technology of thiamphenylphenylserine ethyl ester and glycine ethyl ester hydrochloride, which is applied in the synthesis of p-thymphenylphenylserine ethyl ester and p-thymphenylphenylserine ethyl ester field, which can solve unfavorable esterification Forward progress, unfavorable production rate, cumbersome process and other problems, to achieve the effect of improving reaction efficiency, benefiting environmental protection, and simple operation

Active Publication Date: 2019-10-18
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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Problems solved by technology

[0008] The above three methods all use a large amount of sulfuric acid for catalytic esterification, and a large amount of waste acid is produced during production, which is not conducive to environmental protection; , all need to be very cautious, so as not to cause harm to personnel and equipment, which is not conducive to increasing production rate
[0009] In addition, the above-mentioned method often needs to use p-thiamphenicyl benzaldehyde as the starting material, react with copper sulfate and glycine to generate copper p-thymphenyl phenylserine, and then react with absolute ethanol under the catalysis of concentrated sulfuric acid. After a series of To obtain p-thymphenylphenylserine ethyl ester, two steps are required, and the process is relatively cumbersome
[0010] At the same time, ethanol and sulfuric acid react to form water when heated, which is not conducive to the forward progress of esterification

Method used

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  • The synthetic method of p-thymphenyl phenyl serine ethyl ester and p-thymphenyl phenyl serine ethyl ester
  • The synthetic method of p-thymphenyl phenyl serine ethyl ester and p-thymphenyl phenyl serine ethyl ester

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[0036] The present invention discloses the synthetic method of p-thymphenyl phenyl serine ethyl ester, comprising the following steps:

[0037] S1, add the set dose of glycine ethyl ester hydrochloride and methanol into the reaction kettle, heat up to 30-80°C, preferably between 40-65°C, combine stirring when heating, and make glycine ethyl ester hydrochloride Dissolve in methanol to form the first solution.

[0038] S2, add the set dose of copper sulfate pentahydrate into the first solution to dissolve, and keep stirring at 30-80°C, preferably at 40-65°C for 0.5h to form the second solution, at this time in the second solution The reaction produces glycine ethyl ester copper complex.

[0039] S3, adding an organic base in the second solution, the organic base is preferably one of triethylamine, dimethylamine, and ethylenediamine, so that the pH value of the second solution is adjusted to alkaline reaction conditions, that is: Make the pH value of the second solution between...

Embodiment 1

[0046] Add 500g (15.6mol) of methanol and 73.9g (0.53mol) of ethyl glycine hydrochloride into a 1000ml reaction flask, stir and heat up to 50-55°C to completely dissolve ethyl glycine hydrochloride in methanol to form the first solution.

[0047] Then add 67.5 g (0.27 mol) of copper sulfate pentahydrate into the first solution, stir to dissolve it completely, and continue to keep stirring at 50-55° C. for 0.5 h to obtain the second solution.

[0048]Next, start to add triethylamine dropwise to the second solution to adjust the pH value of the second solution to 8.5-9.0, then add 92 g (0.5 mol) of p-thiamphenicyl benzaldehyde, and keep the reaction at 50-55 ° C for 30 h , control the pH value between 8.5-9.0 during the heat preservation period, during the reaction, monitor the progress of the reaction by HPLC, and when the percentage of p-thiamphenicyl benzaldehyde calculated by the area normalization method <2%, the reaction is considered to be over .

[0049] Recover methan...

Embodiment 2

[0051] Add 500g (15.6mol) of methanol and 76.7g (0.550mol) of ethyl glycine hydrochloride into a 1000ml reaction flask, stir and heat up to 40-45°C to completely dissolve ethyl glycine hydrochloride to form the first solution.

[0052] Then add 71.2 g (0.285 mol) of copper sulfate pentahydrate into the first solution, stir to dissolve it completely, and continue to keep stirring at 40-45° C. for 0.5 h to obtain the second solution.

[0053] Then start to drop dimethylamine methanol solution in the second solution, the pH value of the second solution is adjusted to between 9.0-9.3, then add p-thiamphenicyl benzaldehyde 92g (0.5mol), and at 40-45 ℃ Insulation reaction 30h, control pH value between 9.0-9.3 during the insulation reaction, during the reaction, monitor the progress of the reaction by HPLC, when the percentage content of p-thiamphenicyl benzaldehyde calculated by the area normalization method<2%, The reaction is considered complete.

[0054] Recover methanol by vacu...

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Abstract

The invention discloses a synthetic method of P-methyl sulfone phenyl ethyl serinate, comprising the steps of S1, adding ethyl glycinate hydrochloride into methanol, and heating to dissolve to form afirst solution; S2, adding copper sulfate pentahydrate in the first solution to form a second solution by dissolving; S3, adjusting PH value of the second solution to meet the condition for alkaline reaction, adding P-methylsufonyl benzaldehyde to allow reaction, and holding the temperature and controlling the PH value to keep reaction condition values during reaction; S4, recycling methanol in the reacted materials, adding water to the residue to form a third solution, cooling, and centrifugally separating to obtain P-methyl sulfone phenyl ethyl serinate. The ethyl glycinate hydrochloride andP-methylsufonyl benzaldehyde are subjected to further reaction under the catalytic action of copper sulfate and an organic base to generate a target product; no sulfuric acid is used in the reactionprocess, the amount of waste acid in waste water is decreased, and the environment is protected; dangers that may occur during sulfuric acid transport and production are avoided, better safety is provided, and operating efficiency can be improved.

Description

technical field [0001] The invention relates to a florfenicol intermediate and a synthesis method thereof, in particular to a synthesis method of p-thiamphenylphenylserine ethyl ester with high yield, less waste water and environmental protection and p-thiamphenylphenylserine ethyl ester ester. Background technique [0002] Florfenicol, also known as fluprofen and fluthiamphenicol, is a white or off-white crystalline powder, odorless, and bitter in taste. It is a new type of chloramphenicol for veterinary medicine that was successfully developed in the late 1980s. A class of broad-spectrum antibacterial drugs, which produce broad-spectrum antibacterial effects by inhibiting the activity of peptidyltransferases, and have a broad antibacterial spectrum, including various Gram-positive and negative bacteria and mycoplasma. [0003] It was first launched in Japan in 1990. In 1993, Norway approved the drug to treat salmon furunculosis. In 1995, France, the United Kingdom, Austri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/04C07C317/48
Inventor 余志强徐剑锋曾淼朱家可卫海浩沈洁
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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